Syntheses of (S)-β-pyrazolylalanine and (S)-quisqualic acid from a serine-derived aziridine

Tetrahedron Letters

Volumn 37, Issue 29, 1996, Pages 5225-5226

  Farthing, Christopher N ^a   Baldwin, Jack E ^a   Russell, Andrew T ^a,b   Schofield, Christopher J ^a   Spivey, Alan C ^a,c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF SALFORD   (United Kingdom)

^c UNIVERSITY OF SHEFFIELD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,4 OXADIAZOLIDINE 3,5 DIONE; 3 (1 PYRAZOLYL)ALANINE; ALANINE DERIVATIVE; AZIRIDINE; PYRAZOLE; QUISQUALIC ACID; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; SYNTHESIS;

EID: 0030586053     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01061-1     Document Type: Article

References (17)

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2. 2. See for example: (a) Baldwin, J.E.; Adlington, R.M.; Birch, D.J. J. Chem. Soc., Chem. Commun., 1985, 256.
3. (b) Baldwin, J.E.; Adlington, R.M.; Mellor, L.C. Tetrahedron, 1994, 50, 5049.
4. (c) Arnold, L.D.; May, R.G.; Vederas, J.C. J. Am. Chem. Soc., 1988, 110, 2237.
5. (d) Shiba, T.; Ukita, T.; Mizuno, K.; Teshima, T.; Wakamiya, T. Tetrahadron Lett., 1977, 18, 2681.
6. (e) Imae, K.; Kamachi, H.; Yamashita, H.; Okiti, T.; Okuyama, S.; Tsuno, T.; Yamasaki, T.; Sawada, Y.; Ohbayashi, M.; Naito, T.; Oki, T. J. Antibiot., 1991, 44, 76.
7. 3. Baldwin, J.E.; Farthing, C.N.; Russell, A.T.; Schofield, C.J.; Spivey, A.C. Tetrahedron Lett., 1996, in press.
8. 4. Shinano, S.; Kaya, T. J. Agric. Chem. Soc. Japan, 1957, 31, 759.
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10. 6. Takeshita, M.; Nishizuka, Y.; Hayaishi, O. J. Biol Chem., 1963, 238, 660.
11. 7. Chuan, P.P.; Din, F.S.; Chao, T.C. Scientia Sinica, 1976, 21, 691.
12. 8. Subasinghe, N.; Schultz, M.; Roon, R.J.; Koerner, J.F.; Johnson, R.L. J. Med. Chem., 1992, 35, 4602.
13. 9. Guibourdenche, C.; Roumestant, M.L.; Viallefont, P. Tetrahedron Asymm., 1993, 4, 2041.
14. 10. Bycroft, B.; Chhabra, S.R.; Grout, R.J.; Crowley, P.J. J. Chem. Soc., Chem. Commun., 1984, 1156.
15. 11. Zinner, G.; Stoffel, R. Arch. Pharm., 1969, 302, 691.
16. 12. Available from the Sigma-Aldrich Chemical Co.
17. 13. Racemic aziridine (±)-1 reacted with other nitrogen based nucleophiles to produce β-substituted alanines in good yields. For example, reaction of (±)-1 with sodium azide led to the isolation of protected β-azidoalanine in quantitative yield, and reaction with imidazole resulted in the isolation of protected β-imidazolylalanine in 57% yield.